Radical Photocyclization Route for Macrocyclic Lactone Ring Expansion and Conversion to Macrocyclic Lactams and Ketones
2013
Nishikawa, Keisuke | Yoshimi, Yasuharu | Maeda, Kousuke | Morita, Toshio | Takahashi, Ichiro | Itou, Tatsuya | Inagaki, Sho | Hatanaka, Minoru
A new method for the synthesis of macrocyclic lactones, lactams, and ketones, which utilizes photoinduced intramolecular radical cyclization reactions of substrates containing tethered carboxylic acids and α,β-unsaturated carbonyl moieties, has been uncovered. Photocyclization of the carboxylic acids tethered acrylate ester, which were prepared starting from the macrocyclic lactones, gave the two-carbon elongated macrocyclic lactones via decarboxylation. Similar photoreactions of carboxylic acid tethered acryl amide or α,β-unsaturated ketone moieties, which were also prepared starting from the macrocyclic lactones, produced macrocyclic lactams or ketones, respectively. The simple approach can be readily applied to the preparation of a variety of macrocyclic lactones, lactams, and ketones with tunable ring sizes.
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